(a) The - SH group is sometimes called the mercapto group....

Name: Problem 13, Chapter 14: Organic Chemistry
Uploaded: 2020-09-05T12:13:59-08:00
Duration: 2 min 50 s
Channel: Zubair Abdulla
Description: (a) The - SH group is sometimes called the mercapto group. 6-Mercaptopurine is used in the treatment of acute leukemia. Write its structure. (b) Allopurinol, a compound used to treat gout, is 6-hydroxypurine. Write its structure.

(a) The - SH group is sometimes called the mercapto group. 6-Mercaptopurine is used in the treatment of acute leukemia. Write its structure. (b) Allopurinol, a compound used to treat gout, is 6-hydroxypurine. Write its structure.

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Key Concepts

Hydroxyl Group in Purine Derivatives

A hydroxyl (-OH) substitution at the 6-position of the purine ring, as seen in compounds like 6-hydroxypurine (allopurinol), introduces different chemical properties compared to the mercapto group. This variation in substitution is employed in drug design to target specific enzymes and pathways, thereby yielding distinct therapeutic effects.

Mercapto (-SH) Functional Group

The mercapto group, represented by -SH, is a sulfur-containing functional group used as a substituent on the purine ring in compounds like 6-mercaptopurine. This group can participate in unique chemical reactions and interactions, influencing the molecule’s reactivity and pharmacological profile.

Purine Ring System

The purine ring system is a bicyclic aromatic heterocycle that consists of a pyrimidine ring fused to an imidazole ring. It forms the core structure of many important biomolecules, including nucleobases like adenine and guanine, and serves as a scaffold for numerous pharmacologically active compounds.

Positional Substitution on Purines

Purines can be functionally modified by substituting various groups at specific positions on the ring, such as the 6-position. These substitutions can significantly alter the biological activity of the molecule and are crucial for structure-activity relationships in medicinal chemistry.

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